An oxygen-containing compound such as an alcohol compound, a ketone compound, an aldehyde compound and a carboxylic acid compound obtained by oxidizing a methyl or methylene group of an olefin compound having carbon-carbon double bond which is bonded to the methyl or methylene group such as a 1-propenyl, 2-propenyl and 2-methyl-1-propenyl group (hereinafter simply referred to as the olefin compound), is very important compound as various chemicals and synthetic intermediate of them. For example, 3,3-dimethyl-2-E-(2-carboxy-1-propenyl)cyclopropanecarboxylic acid esters obtained by oxidizing a methyl group of 2-methyl-1-propenyl group of 3,3-dimethyl-2-(2-methyl-1-propenyl)cyclopropanecarboxylic acid esters is an important chrysanthemic acid derivative as an acid part of household agents for epidemic prevention and insecticides which is known as pyrethrates (e.g. Synthetic Pyrethroid Insecticides: Structure and Properties, 3 (1990)). E,E-2,6-dimethyl-2,6-octadiene-1,8-diol-8-acetate, which is obtained by oxidizing a terminal methyl group of geranyl acetate, is useful as an intermediate in natural-product synthesis (e.g. Tetrahedron Letters, 42, 2205 (2001)).
A methyl or methylene group which is bonded to a carbon-carbon double bond of an olefin compound is the methyl or methylene group at allylic position. As a method for producing an oxygen-containing compound by oxidizing the methyl or methylene group at allylic position, for example, method for reacting the above-mentioned olefin compound with selenium dioxide (e.g. Comprehensive Organic Synthesis, 7, 83 (1991) and Proc. Japan Acad., 32, 353 (1956)) and method for reacting an olefin compound with an organic hydroperoxide in the presence of selenium dioxide catalyst (e.g. J. Amer. Chem. Soc., 99, 5526 (1977)) are known. However, in the former method, a large amount of selenium dioxide is used and it is necessary to oxidize the selenium metal again for reuse since they are converted to selenium metal after completion of the reaction. In the latter method, methylene chloride, which has some problems on the occupational safety and health, is used as a solvent and it is difficult to recover and reuse of selenium dioxide catalyst. Neither method was satisfactory industrially.